A product of Dundee United's youth development system, Watson turned professional in 2006 and made his first team debut in January 2007. His early career was disrupted by injury problems, and he spent periods on loan to Forfar Athletic and East Fife before establishing himself in the Dundee United team in 2010; he was a member of the squad that won the Scottish Cup that year. Since then, Watson has established himself as a regular in the right back position, making his 100th league appearance in February 2014. He is a former Scotland under-19 internationalist.

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Watson was born and brought up in Livingston, where he attended Deans Community High School.[1] He played for Livingston Star Boys Club, a youth team run by his father, before joining the Dundee United youth system at under-14 level.[1] He was included in the club's first team squad whilst still a youth signing, being an unused substitute for United's last two matches of the 2005-06 season.[1] After signing his first professional contract in December 2006, Watson's debut for the Dundee United first team came in the Scottish Cup third round match against St Mirren in January 2007, when he played 85 minutes in a 3–2 victory. Following this victory, he was described by his then manager Craig Levein as "without fear of contradiction, the best young player I have ever worked with".[2]

Watson, who made his first league appearance as a late subsititute in March 2007, was due to start in the match against Celtic shortly afterwards but suffered a dislocated knee during the warm-up.[3] Having featured in a handful of reserve matches throughout September 2008, manager Craig Levein stated he would be sent out on loan to continue his build-up to full fitness[4] and was loaned to Forfar for a month in January 2009. Suffering another knee dislocation in a practice match after playing his first match for Forfar, Watson's loan was extended after it was revealed he would return to playing within weeks,[5]

In 2009, Watson agreed a contract extension with United until May 2012,[6] going out on loan again in December to East Fife.[7]

After returning from loan in March 2010, Watson was brought on as a 47th minute substitute for Michael Kovacevic in a 1–0 Scottish Cup victory over Rangers. This opportunity lead to 11 appearances in the remainder of the season, culminating in a 3–0 Scottish Cup Final victory over Ross County on 15 May 2010.

The 2010–11 season saw a breakthrough to regular first team football for Watson, making 34 appearances in total. His first goal was marked against Motherwell in a 4–0 win at Tannadice Park on 7 May 2011, where he also won man of the match.[8] He scored his second Dundee United goal on 17 March 2012 against Rangers.[9]

On 28 January 2015, Watson signed for Hibernian on loan until the end of the season to provide further defensive cover for the Edinburgh side.[10]